Reaktion #166176

Reaktionsgleichung

8-(1,1′-binaphthyl-2-yl)-7,7,9,9-tetramethyl-1,4-dioxa-8-phosphaspiro[4.5]decane

triethylamine

bromobenzene

diethylphosphite

→

Diethyl phenylphosphonate

Ausbeute 59.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar
2. 2
   SonstigeThe vial was sealed with a crimp top
3. 3
   Sonstigethe vial was removed from the heating block
4. 4
   Temperaturcooled to room temperature
5. 5
   workup.ADDITIONThe reaction solution was diluted with tetrahydrofuran (2 mL)
6. 6
   Filtrationfiltered into a tared 125-mL Erlenmeyer flask
7. 7
   WaschenThe vial was rinsed with tetrahydrofuran (5×1 mL)
8. 8
   Waschenby washing of the filter cake with tetrahydrofuran (5 mL)

Vorschrift

In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar was charged with palladium(II) acetate (1.4 mg, 0.00637 mmol, 0.02 equivalents), 8-(1,1′-binaphthyl-2-yl)-7,7,9,9-tetramethyl-1,4-dioxa-8-phosphaspiro[4.5]decane (3.6 mg, 0.00764 mmol, 0.024 equivalents) and ethanol (0.64 mL). To the slurry were added triethylamine (67 μL, 0.478 mmol, 1.5 equivalents), bromobenzene (34 μL, 0.318 mmol, 1 equivalent) and diethylphosphite (49 μL, 0.382 mmol, 1.2 equivalents). The vial was sealed with a crimp top and stirred at 80° C. After 24 hours, the vial was removed from the heating block, cooled to room temperature and brought out of the glovebox. The reaction solution was diluted with tetrahydrofuran (2 mL) and filtered into a tared 125-mL Erlenmeyer flask. The vial was rinsed with tetrahydrofuran (5×1 mL), followed by washing of the filter cake with tetrahydrofuran (5 mL). A wt % analysis was performed on the filtrate and an assay yield of 59% was measured versus commercially available diethyl phenylphosphonate.

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